5-氰基吲哚酮 | 61394-50-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 5-氰基吲哚酮
• 中文别名: 5-氰基-1,3-二氢吲哚-2-酮；5-氢基吲哚
• 英文名称: 2-oxo-2,3-dihydro-1H-indole-5-carbonitrile
• 英文别名: 2-oxoindoline-5-carbonitrile；2-oxo-1,3-dihydroindole-5-carbonitrile
• CAS: 61394-50-1
• 化学式: C₉H₆N₂O
• mdl: MFCD02179599
• 分子量: 158.159
• InChiKey: NZOSLRYUVHMXTQ-UHFFFAOYSA-N

物化性质

• 熔点：
  236-239°C
• 沸点：
  389.7±42.0 °C(Predicted)
• 密度：
  1.33

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/21/22
• 海关编码：
  2933790090
• 危险品运输编号：
  UN 3439
• 危险性防范说明：
  P260,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H315,H317,H319,H335
• 储存条件：
  存储条件：室温、密封、干燥

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 5-Cyanooxindole
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 5-Cyanooxindole
CAS number: 61394-50-1

---

Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C9H6N2O
Molecular weight: 158.2

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-氰基吲哚酮 在 sodium hydroxide 、 水 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 2-hydroxy-3-{5-[(4-methylpiperazin-1-yl)sulfonyl]pyridin-2-yl}-1H-indole-5-carboxylic acid
  参考文献：
  名称：

  [EN] 3-HETEROCYCLYL-INDOLE DERIVATIVES AS INHIBITORS OF GLYCOGEN SYNTHASE KINASE-3 (GSK-3)
  [FR] NOUVEAUX COMPOSES

  摘要：

  公开号：

  WO2005027823A3
• 作为产物：
  描述：

  3-氟-4-硝基苯腈 在 potassium carbonate 、 lithium chloride 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 5-氰基吲哚酮
  参考文献：
  名称：

  取代 oxindol-3-ylidenes 作为 AMP 激活蛋白激酶 (AMPK) 抑制剂。

  摘要：

  AMP 激活蛋白激酶 (AMPK) 是一种中央代谢调节因子，可促进缺氧下癌症的生长和存活，并在维持癌症干细胞中发挥作用。探究 AMPK 靶向治疗癌症的潜力的一个主要挑战是缺乏有效且选择性的小分子抑制剂。化合物 C 已广泛用作 AMPK 抑制剂，但它缺乏效力且选择性较差。多激酶抑制剂舒尼替尼已证明对 AMPK 活性具有有效的纳摩尔抑制作用，并且具有改进的空间。在这里，我们设计并合成了几个系列的羟吲哚，以确定 AMPK 抑制的结构要求并提高选择性。我们鉴定了两种有效的新型基于羟吲哚的 AMPK 抑制剂，它们被设计为与 AMPK ATP 结合位点中的 DFG 基序相互作用，这一关键特征避免了与舒尼替尼的常见受体酪氨酸激酶靶点的相互作用。通过抑制髓系白血病细胞中乙酰辅酶A羧化酶（ACC）（AMPK的已知底物）的磷酸化，证实了这些羟吲哚与AMPK的细胞结合。有趣的是，尽管 AMPK 在 K562 细胞中高度表达和激活，但这些基于羟吲哚的

  DOI：

  10.1016/j.ejmech.2020.112316

文献信息

• Dihydroindolone compounds, a process for their preparation and pharmaceutical compositions containing them
  申请人：Ortuno Jean-Claude

  公开号：US20110034460A1

  公开（公告）日：2011-02-10

  Compounds of formula (I): wherein: m and n represent 1 or 2, A represents a pyrrolyl group, X represents a C(O), S(O) or SO 2 group, R 1 and R 2 represent an alkyl group or, together with the nitrogen atom carrying them, form a heterocyclic group, R 3 and R 4 , together with the atoms carrying them, form a heterocyclic group, R 5 represents a hydrogen atom or an alkyl group, R 6 represents a hydrogen atom or a halogen atom. Medicinal products containing the same which are useful in treating cancer.

  式（I）的化合物： 其中： m和n代表1或2， A代表吡咯基， X代表C（O）、S（O）或SO2基团， R1和R2代表烷基或与携带它们的氮原子一起形成杂环基团， R3和R4与携带它们的原子一起形成杂环基团， R5代表氢原子或烷基， R6代表氢原子或卤素原子。 含有这些化合物的药物，可用于治疗癌症。
• [EN] OXINDOLYL INHIBITOR COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS DE L'OXINDOLYLE
  申请人：GILEAD COLORADO INC

  公开号：WO2010009166A1

  公开（公告）日：2010-01-21

  A compound of general Formula (I) having histone deacetylase (HDAC) and/or CDK inhibitory activity, a pharmaceutical composition comprising the compound, and a method useful to treat diseases using the compound. (Formula should be inserted here) Formula (I)

  具有组蛋白去乙酰化酶（HDAC）和/或CDK抑制活性的一种通用化合物（I）的化合物，包括该化合物的药物组合物，以及使用该化合物治疗疾病的有效方法。（应在此处插入公式）公式（I）
• Oxindole derivatives
  申请人：Zeneca Limited

  公开号：US06265411B1

  公开（公告）日：2001-07-24

  The invention relates to compounds of formula (I), wherein: R2 represents hydroxy, halogeno, C1-3alkyl, C1-3alkoxy, C1-3alkanoyloxy, trifluoromethyl, cyano, amino, nitro, C2-4alkanoyl, C1-4alkanoylamino, C1-4alkoxycarbonyl, C1-4alkylthio, C1-4alkylsulphinyl, C1-4alkylsulphonyl, carbamoyl, overscore (N)}—C1-4alkylcarbamoyl, overscore (N)},overscore (N)}-di(C1-4alkyl)carbamoyl, aminosulphonyl, overscore (N)}—C1-4alkylaminosulphonyl, overscore (N)},overscore (N)}-di(C1-4alkyl)aminosulphonyl, C1-4alkylsulphonylamino, or a group R4X1 wherein X1 represents a direct bond, C2-4alkanoyl, —CONR5R6—, —SO2NR7R8— or —SO2R9— (wherein R5 and R7, each independently represents hydrogen or C1-2alkyl and R6, R8 and R9 each independently represents C1-4alkyl and wherein R4 is linked to R6, R8 or R9) and R4 represents an optionally substituted group selected from phenyl and a 5 or 6-membered heterocyclic group; n is an integer from 0 to 4, R1 represents hydrogen, C1-4alkyl, C1-4alkoxymethyl, di(C1-4alkoxy)methyl or C1-4alkanoyl; m is an integer from 0 to 4; and R3 represents hydroxy, halogeno, nitro, trifluoromethyl, C1-3alkyl, cyano, amino or R10X2 (wherein X2 represents a direct bond, —CH2—, or a single or double heteroatom linker group including —S—, —SO— and —NR15— (wherein R15 represents hydrogen, C1-3alkyl or C1-3alkoxyC2-3alkyl), and R10 is an alkenyl or alkynyl chain optionally substituted by for example hydroxy, amino, nitro, alkyl, cycloalkyl, alkoxyalkyl, or an optionally substituted group selected from pyridone, phenyl and a heterocyclic ring, which alkyl, alkenyl or alkynyl chain may have a heteroatom linker group, or R10 is an optionally substituted group selected from pyridone, phenyl and a heterocyclic ring. The compounds of formula (I) and the pharmaceutically acceptable salts thereof inhibit the effects of VEGF and FGF, properties of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.

  本发明涉及公式(I)的化合物，其中：R2代表羟基，卤素，C1-3烷基，C1-3烷氧基，C1-3烷氧酰基，三氟甲基，氰基，氨基，硝基，C2-4烷氧酰基，C1-4烷氧酰氨基，C1-4烷氧羰基，C1-4烷基亚硫酰基，C1-4烷基亚磺酰基，C1-4烷基亚磺酰基，碳酸酰基，N}-C1-4烷基碳酸酰基，N},N}-二(C1-4烷基)碳酸酰基，氨基磺酰基，N}-C1-4烷基氨基磺酰基，N},N}-二(C1-4烷基)氨基磺酰基，C1-4烷基亚磺酰氨基，或R4X1基团，其中X1代表直接键，C2-4烷氧酰基，-CONR5R6-，-SO2NR7R8-或-SO2R9-（其中R5和R7，每个独立地代表氢或C1-2烷基，R6，R8和R9每个独立地代表C1-4烷基，R4连接到R6，R8或R9），R4代表可选地取代的基团，选自苯基和5或6成员的杂环组；n是0到4的整数，R1代表氢，C1-4烷基，C1-4烷氧甲基，二(C1-4烷氧基)甲基或C1-4烷氧酰基；m是0到4的整数；R3代表羟基，卤素，硝基，三氟甲基，C1-3烷基，氰基，氨基或R10X2（其中X2代表直接键，-CH2-，或包括-S-，-SO-和-NR15-的单个或双杂原子连接基团（其中R15代表氢，C1-3烷基或C1-3烷氧基C2-3烷基），R10是可选地取代的烯基或炔基链，例如羟基，氨基，硝基，烷基，环烷基，烷氧基烷基，或从吡啶酮，苯基和杂环环中选择的可选地取代的基团，该烷基，烯基或炔基链可具有杂原子连接基团，或R10是可选地取代的基团，选自吡啶酮，苯基和杂环环。公式(I)的化合物及其药用盐抑制VEGF和FGF的活性，这些活性在包括癌症和类风湿性关节炎在内的多种疾病状态的治疗中具有重要价值。
• [EN] OXINDOLE COMPOUNDS CARRYING A NITROGEN-BOUND SPIRO SUBSTITUENT AND USE THEREOF FOR TREATING VASOPRESSIN-RELATED DISEASES<br/>[FR] COMPOSÉS D'OXINDOLE PORTANT UN SUBSTITUANT SPIRO LIÉ À UN ATOME D'AZOTE, ET LEUR UTILISATION POUR LE TRAITEMENT DE MALADIES LIÉES À LA VASOPRESSINE
  申请人：ABBVIE DEUTSCHLAND

  公开号：WO2015173393A1

  公开（公告）日：2015-11-19

  The present invention relates to novel substituted oxindole derivatives of the formula I wherein A is a ring selected from phenyl and 6-membered hetaryl containing 1 or 2 nitrogen atoms as ring members, where ring A carries one substituent R6 and optionally one substituent R7;B is a ring selected from phenyland a monocyclic or bicyclic het- eroaromatic ring containing 1, 2 or 3 heteroatoms selected from O, N and S as ring members, where ring B may carry 1, 2 or 3 substituents R8;X1, X2, X3 and X4, independently of each other, are selected from -CH2-, -O-, -S(O)c-, -NH-, -C(O)-, -CH2CH2-,-CH2O-, -OCH2-, -S(O)cCH2-, -CH2S(O)c-, CH2NH-,-NHCH2-, -CH2C(O)-andC(O)CH2-;X5 is NH,CH2or O,;and wherein c, R1, R2, (R3)a, (R4)b, R5, R6, R7, and R8 are as defined in the claims. The present invention also relates to pharmaceutical compositions comprising the novel substituted oxindole derivatives of the formula I, and to their use for the treatment of vasopressin-related disorders.

  本发明涉及一种新型的氧吲哚衍生物，其化学式为I，其中A是从苯基和含有1或2个氮原子作为环成员的6元杂环中选择的环，其中环A携带一个取代基R6和可选的一个取代基R7；B是从苯基和含有1、2或3个氧、氮和硫原子作为环成员的单环或双环杂芳环中选择的环，其中环B可能携带1、2或3个取代基R8；X1、X2、X3和X4，彼此独立地从-CH2-、-O-、-S(O)c-、-NH-、-C(O)-、-CH2CH2-、-CH2O-、-OCH2-、-S(O)cCH2-、-CH2S(O)c-、CH2NH-、-NHCH2-、-CH2C(O)-和C(O)CH2-中选择；X5是NH、CH2或O；其中c、R1、R2、(R3)a、(R4)b、R5、R6、R7和R8如权利要求中所定义。本发明还涉及包含化学式I中的新型氧吲哚衍生物的药物组合物，以及它们用于治疗与加压素相关的疾病。
• [EN] COMPOUNDS FOR MODULATING S1P1 ACTIVITY AND METHODS OF USING THE SAME<br/>[FR] COMPOSÉS POUR MODULER L'ACTIVITÉ DE S1P1 ET LEURS PROCÉDÉS D'UTILISATION
  申请人：TREVENA INC

  公开号：WO2018231745A1

  公开（公告）日：2018-12-20

  The present embodiments are directed, in part, to compounds, or pharmaceutically acceptable salts thereof, or pharmaceutical compositions thereof for modulating the activity of S1P1 receptor and methods of using the same.

  目前的实施例部分涉及化合物，或其药学上可接受的盐，或用于调节S1P1受体活性的药物组合物，以及使用它们的方法。

表征谱图